Chester Islands Holiday Rentals

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Holiday Rentals in Chester Islands

Oakhill Pines Campground

3.0 star property
8.8 out of 10, Excellent, (15)
"Great place"
Oakhill Pines Campground

Black Forest Cabins

3.0 star property
10.0 out of 10, Exceptional, (9)
"Great spot for a special night out … beds were super comfortable "
The price is AU$304
includes taxes & fees
2 Nov - 3 Nov
Black Forest Cabins

Juniper Bell Tent near Peggy's Cove

8.8 out of 10, Excellent, (3)
"Good for a nights stay and close to Peggy’s cove. Comfy and enough space"
The price is AU$222
includes taxes & fees
6 Oct - 7 Oct
Juniper Bell Tent near Peggy's Cove

Oceanfront Cottage on a Quiet Cove Just Outside Lunenburg

10.0 out of 10, Exceptional, (111)
"I wish we had more time to enjoy the cottage. There was so much to see in area, we were busy all day, but a comfy place to come home too. "
Oceanfront Cottage on a Quiet Cove Just Outside Lunenburg

One bedroom fully equipped Mahone Bay luxury cottage

10.0 out of 10, Exceptional, (101)
"Great cottage to use as a base to discover the area. Well equipped, quiet and close to restaurants and shopping."
The price is AU$300
includes taxes & fees
13 Oct - 14 Oct
One bedroom fully equipped Mahone Bay luxury cottage

Oceanfront Garden Cottage - Gateway to Attractions & Towns. Private Cove Mooring

9.6 out of 10, Exceptional, (34)
"Beautiful setting, very peaceful with lovely linens on the beds. The kitchen is fully stocked, the sitting room is comfortable and the outside decks are amazing. The little village of Chester was close by with a cozy pub offering live music on select nights and the local playhouse had local talent performing while we were there. We would stay again"
Oceanfront Garden Cottage - Gateway to Attractions & Towns. Private Cove Mooring

Pebble Oceanside RV Retreat – Waterfront Hot Tub & Deck

10.0 out of 10, Exceptional, (3)
"Beautiful location on the water, super friendly hosts. Location close to so many little towns with great food and amazing people. Trailer has everything that you need for your stay, they thought of everything. They made us feel welcome and we will be back for sure. We took our paddleboards out; he even lent us a fishing rod to use on the nearby Warf. "
Pebble Oceanside RV Retreat – Waterfront Hot Tub & Deck

Whalesback Cottage, on the ocean with access to Peggys Cove Preservation Area

9.8 out of 10, Exceptional, (124)
"Cozy cottage with wonderful views. "
Whalesback Cottage, on the ocean with access to Peggys Cove Preservation Area

Oceanside Cottage, Spectacular Sunsets, near Peggy's Cove

10.0 out of 10, Exceptional, (85)
"Everything about our trip and this property was amazing. The location, the peace, the scenery, etc. exceeded our expectations. The house was perfect and so comfortable. We hope to be back soon! "
Oceanside Cottage, Spectacular Sunsets, near Peggy's Cove

Ocean front cottage, relax and enjoy the sunset over St. Margaret's Bay!

10.0 out of 10, Exceptional, (34)
"Very nice spot. property nicely decorated and conveniet"
Ocean front cottage, relax and enjoy the sunset over St. Margaret's Bay!

Overlooking the Stunning views of St.Margaret's Bay

9.8 out of 10, Exceptional, (18)
"Comfortable, relaxing place to stay that has great views and perfect location to visit different areas!"
The price is AU$430
includes taxes & fees
3 Oct - 4 Oct
Overlooking the Stunning views of St.Margaret's Bay

Moonlight Cottage

9.2 out of 10, Wonderful, (15)
"Great time, went Peggy’s cove, Hubbard farm market, lunenburg and mahone bay"
Moonlight Cottage

Oceanfront 3-Bedroom Captain's House

9.8 out of 10, Exceptional, (27)
"Perfect house, perfect location, fabulous area to vacation!"
Oceanfront 3-Bedroom Captain's House

Family Home In the Heart of the Village of Chester

9.6 out of 10, Exceptional, (28)
"Spacious, clean, comfortable, and lots of room for people to spread out. We would happily return."
Family Home In the Heart of the Village of Chester

Wilson's Coastal Club - C3

10.0 out of 10, Exceptional, (6)
"Nice place, close to the water with a small private beach"
The price is AU$266
includes taxes & fees
7 Oct - 8 Oct
Wilson's Coastal Club - C3

Mahone Bay Hide-Away

10.0 out of 10, Exceptional, (90)
"Loved this property. So cute and so very clean! Beautifully decorated and very well appointed. Walkable to great restaurants and coffee shops. Loved Mahone Bay and hope to be back. Will definitely stay at this wonderful cottage. "
The price is AU$299
includes taxes & fees
3 Oct - 4 Oct
Mahone Bay Hide-Away

The Land Yacht – Indoor Pool, Hot Tub, Solarium Lounge & Sublime Ocean Views

9.8 out of 10, Exceptional, (221)
"Lots of amenities. Owners very helpful in recommending local restaurants. Enjoyed finding mussels and sea glass on the little beach as well as the antics of the "rock" beavers. The heated pool was a plus. Absolutely wonderful views of the bay."
The Land Yacht – Indoor Pool, Hot Tub, Solarium Lounge & Sublime Ocean Views

Oceanfront Luxury Magical Views Sunset and Sunrise

9.6 out of 10, Exceptional, (18)
"We took day trips from Holly’s home all week, but the view off the balcony was a delight to return to. "
Oceanfront Luxury Magical Views Sunset and Sunrise

Unique Ocean View Hilltop Retreat

10.0 out of 10, Exceptional, (175)
"Great hosts and amazing location"
Unique Ocean View Hilltop Retreat

4 bed ,2 bathroom home. 2 of the 4 bedrooms are slightly smaller . Still comfort

8.4 out of 10, Very good, (27)
"Beautiful view, the property owner was very responsive, they even had water in the fridge. Was perfect for our relaxing family getaway! "
The price is AU$260
includes taxes & fees
7 Oct - 8 Oct
4 bed ,2 bathroom home. 2 of the 4 bedrooms are slightly smaller . Still comfort
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Chester Islands Hotel Reviews

Find out more about Chester Islands

Find out more about Chester Islands

Everything you need to know about Chester Islands holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Chester Islands holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Chester Islands holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Chester Islands holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Chester Islands. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Chester Islands holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Chester Islands holiday rentals we have selected for you start as low as AU$222 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Chester Islands rentals

At Expedia, we put the best Chester Islands holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Chester Islands rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Chester Islands holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Chester Islands. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Can I find holiday rentals in Chester Islands?

Yes, there are holiday rentals close to the most popular sights in Chester Islands, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Chester Islands has to offer?

Family Home In the Heart of the Village of Chester: This holiday home rental outside of Chester Islands is located near the beach, and has a balcony, a garden and a BBQ to put you at ease in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Make the most of books in this rental home to help you unwind.

What’s there to see and do in Chester Islands?

Explore the area and family-friendly sights such as Shore Club Dance Hall, or get out into nature at a spot like Graves Island Provincial Park. In the wider area, you’ll find Chester Golf Club and Chester Playhouse.

What’s a holiday rental in Chester Islands like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Chester Islands. Holiday rentals offer amenities such as kitchens and laundry facilities so you'll have all the comforts of home. If you're concerned about cleanliness, a holiday rental can offer a sense of security away from public hotel lifts and busy front desks while still allowing you to travel. You'll also get more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a great choice for a family getaway.